I've worn similar boots backpacking in Glacier and Rocky Mountains NPs (5-6 days out) with no issues. I always bring a pair of sandals along so I can take my boots off once at the site so they can breath/dry.

The main problem is they're heavy, but if you're comfortable walking in them for long distances I would think they'll be fine (assuming you're talking about ones with the Vibram sole not the cork or crepe). A good pair of merino socks and comfortable insoles definately doesn't hurt either.

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Doing a trip to Vancouver/Seattle/Portland in late February and planning to go up to Whistler, as well as some hiking here and there.

Was eyeing the Hoka One One Ultra Tor Hi boots, but is it really necessary to have waterproof boots? Don't want to spend that much for only a couple of weeks wear, especially since I live in warmer climates usually..

Would I be able to get away with my Red Wing leather lace up boots ?

In the summer (or late spring / early fall), you'd be fine, but winter is extremely wet so trails will be beyond muddy and you'll hit some snow if you do any serious hikes so I would think you'd do a lot better with proper waterproofed boots.

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Any advice on new goretex vs vintage? I have a mix of paclite, pro shell, new and older jackets and 1 pair of vintage goretex trousers, all seem to have different material qualities and variagated waterproof/breathability ratios, but I can't find a clear pattern - some vintage stuff seriously outperforms modern, and vice versa